alpha-OLEFIN MALEIC ACID OR MALEIMIDE COPOLYMERS FOR ENHANCED BIOACTIVITY

Patent metadata

Field	Value
Publication number	US-2025051503-A1
Application number	US-202218717548-A
Country	US
Kind code	A1
Filing date	Dec 8, 2022
Priority date	Dec 8, 2021
Publication date	Feb 13, 2025
Grant date	—

Abstract

α-Olefin maleic acid copolymers and α-olefin-co-maleimide copolymers have the CH2—CH of the α-olefin in the backbone of the copolymer with the maleic acid or maleimide and the remainder thereof extending from the backbone. The α-olefin having the formula CH2— CH—(CH2)X-R1, and x being in the range of 1 to 19, y and z have a ratio in a range of 0.25: 1 to 8: 1, and n R1 yields a copolymer having an average molecular weight of less than 500 kg/mol. R1 (and R2 in the case of the α-olefin-co-maleimide copolymers) is/are selected from a diverse group of moieties. The α-olefin maleic acid copolymers and α-olefin-co-maleimide copolymers each form lipid particles where the lipid can be from a galactolipid rich membrane of a cyanobacterium.

First claim

1 . An α-olefin modified maleic acid copolymer comprising:
a general formula I

wherein x is in a range of 1 to 19; y and z have a ratio in a range of 0.25:1 to 8:1; n yields a copolymer having an average molecular weight of less than 500 kg/mol; and R 1 is selected from the group consisting of
i. a linear alkane chain, optionally, containing or terminating with a cyclic carbon,
xi. a linear chain alkoxy alkane of the formula —(CH 2 ) q O(CH 2 ) r CH 3 where q is 1 to 5 and r is 1 to 15,
xii. an alkoxy alkane containing or terminating with a cyclic carbon chain,
xiii. a halogenated alkane,
xiv. a halogenated cycloalkane,
xv. a halogenated arene,
xvi. a chain containing a repeating sequence of (CH 2 CH 2 O) t terminating with —OR 2 wherein t equals a value of 1 to 50 and R 2 is hydrogen, a linear alkane, a cyclic alkane, a trifluoromethyl, a halogenated alkane, a halogenated cycloalkane, or a halogenated arene,
xvii. a hydrogen, and
xviii. mixtures thereof.

2 . The α-olefin maleic acid copolymer of claim 1 , wherein x is 5, 7, 9, 11, or 13.

3 . The α-olefin maleic acid copolymer of claim 1 , wherein x is 11 and R 1 is a methyl.

4 . The α-olefin maleic acid copolymer of claim 3 , wherein the average molecular weight is greater than 2 kg/mol but less than 6 kg/mol.

5 . The α-olefin maleic acid copolymer of claim 1 , wherein the halogenated alkane is trifluoromethyl.

6 . The α-olefin maleic acid copolymer of claim 1 , wherein R 1 is one or more of a methyl, a cyclohexane, a benzyl, a norbornyl, or a trifluoromethyl group.

7 . The α-olefin maleic acid copolymer of claim 1 , wherein y and z have a ratio of 1:1.2.

8 . A α-olefin maleic acid copolymer lipid particle comprising:
a lipid from a phospholipid rich membrane or a galactolipid rich membrane- and a modified maleic acid copolymer comprising:
a general formula I

wherein x is in a range of 1 to 19; y and z have a ratio in a range of 0.25:1 to 8:1; n yields a copolymer having an average molecular weight of less than 500 kg/mol; and R 1 is selected from the group consisting of
ii. an alkane chain, optionally, containing or terminating with a cyclic carbon,
xix. a linear chain alkoxy alkane of the formula —(CH 2 ) q O(CH 2 ) r CH 3 where q is 1 to 5 and r is 1 to 15,
xx. an alkoxy alkane containing or terminating with a cyclic carbon chain,
xxi. a halogenated alkane,
xxii. a halogenated cycloalkane,
xxiii. a halogenated arene,
xxiv. a chain containing a repeating sequence of (CH 2 CH 2 O) t terminating with —OR 2 wherein t equals a value of 1 to 50 and R 2 is hydrogen, a linear alkane, a cyclic alkane, a trifluoromethyl, a halogenated alkane, a halogenated cycloalkane, or a halogenated arene,
xxv. a hydrogen, and
xxvi. mixtures thereof:

or a general formula II

wherein x is in a range of 1 to 19; y and z have a ratio in a range of 0.25:1 to 8:1; n yields a copolymer having an average molecular weight of less than 500 kg/mol; and R 1 and R 4 are both selected from the group consisting of
i. a linear alkane chain, optionally, containing or terminating with a cyclic carbon,
ii. a linear chain alkoxy alkane of the formula —(CH 2 ) q O(CH 2 ) r CH 3 where q is 1 to 5 and r is 1 to 15,
iii. an alkoxy alkane containing or terminating with a cyclic carbon chain,
iv. a halogenated alkane,
v. a halogenated cycloalkane,
vi. a halogenated arene,
vii. a chain containing a repeating sequence of (CH 2 CH 2 O) t terminating with —OR 5 wherein t equals a value of 1 to 50 and R 5 is hydrogen, a linear alkane, a cyclic alkane, a trifluoromethyl, a halogenated alkane, a halogenated cycloalkane, or a halogenated arene,
viii. a hydrogen, and
ix. mixtures thereof, and

R 1 and R 4 are the same or different.

9 . The α-olefin maleic acid copolymer lipid particle of claim 8 , wherein the lipid is from a galactolipid rich membrane of a cyanobacterium.

10 . The α-olefin maleic acid copolymer lipid particle of claim 9 , wherein the cyanobacterium is Thermosynechococcus elongatus.

11 . An α-olefin-co-maleimide copolymer comprising:
a general formula II

wherein x is in a range of 1 to 19; y and z have a ratio in a range of 0.25:1 to 8:1; n yields a copolymer having an average molecular weight of less than 500 kg/mol; and R 1 and R 2 are both selected from the group consisting of
x. a linear alkane chain, optionally, containing or terminating with a cyclic carbon,
xi. a linear chain alkoxy alkane of the formula —(CH 2 ) q O(CH 2 ) r CH 3 where q is 1 to 5 and r is 1 to 15,
xii. an alkoxy alkane containing or terminating with a cyclic carbon chain,
xiii. a halogenated alkane,
xiv. a halogenated cycloalkane,
xv. a halogenated arene,
xvi. a chain containing a repeating sequence of (CH 2 CH 2 O) t terminating with —OR 2 wherein t equals a value of 1 to 50 and R 2 is hydrogen, a linear alkane, a cyclic alkane, a trifluoromethyl, a halogenated alkane, a halogenated cycloalkane, or a halogenated arene,
xvii. a hydrogen, and
xviii. mixtures thereof, and

R 1 and R 2 are the same or different.

12 . The α-olefin-co-maleimide copolymer of claim 11 , wherein x is 5, 7, 9, 11, or 13.

13 . The α-olefin-co-maleimide copolymer of claim 11 , wherein x is 11 and R 1 is a methyl.

14 . The α-olefin-co-maleimide copolymer of claim 13 , wherein the average molecular weight is greater than 2 kg/mol but less than 6 kg/mol.

15 . The α-olefin-co-maleimide copolymer of claim 11 , wherein the halogenated alkane is trifluoromethyl.

16 . The α-olefin-co-maleimide copolymer of claim 11 , wherein R 1 is one or more of a methyl, a cyclohexane, a benzyl, a norbomyl, or a trifluoromethyl group.

17 . The α-olefin-co-maleimide copolymer of claim 11 , wherein y and z have a ratio of 1:1.2.

18 - 20 . (canceled)

21 . The α-olefin maleic acid copolymer lipid particle of claim 8 , wherein x is 5, 7, 9, 11, or 13.

22 . The α-olefin maleic acid copolymer lipid particle of claim 21 , wherein x is 11, and R 1 is a methyl.

23 . The α-olefin maleic acid copolymer lipid particle of claim 8 , wherein R 1 is one or more of a methyl, a cyclohexane, a benzyl, a norbornyl, or a trifluoromethyl group.

Assignees

• Univ Tennessee Res Found

Inventors

• Long Brian
• Brady Nathan G
• Bruce Barry D
• Workman Cameron Edward

Classifications

• C08F222/402

  Alkyl substituted imides · CPC title

• C08F8/32

  by reaction with amines · CPC title

• C08F210/04

  Monomers containing three or four carbon atoms · CPC title

• C08F210/14

  Monomers containing five or more carbon atoms · CPC title

• C08F222/02 Primary

  Acids; Metal salts or ammonium salts thereof {, e.g. maleic acid or itaconic acid} · CPC title